Synthesis of 1,3-diazaspiro[5,5]undecanes and 1-thia-3-azaspiro[5,5]undec-2-enes by reaction of 2-cyanocyclohexylideneacetyl isothiocyanate with amines and sodium hydrogen sulfide

1987 ◽  
Vol 52 (4) ◽  
pp. 989-994 ◽  
Author(s):  
Milan Dzurilla ◽  
Ondrej Forgáč ◽  
Peter Kutschy ◽  
Pavol Kristian ◽  
Dušan Koščík ◽  
...  
Keyword(s):  
Hydrogen Sulfide ◽  
Alkaline Medium ◽  
Mass Spectroscopy ◽  
Aromatic Amines ◽  
Secondary Amines ◽  
H Nmr ◽  
Sodium Hydrogen ◽  
Elemental Analyses ◽  
Primary Aromatic Amines ◽  
C Nmr

2-Cyanocyclohexylideneacetyl isothiocyanate (II) reacts with sodium hydrogen sulfide to give 1-thia-3-azaspiro[5,5]undecane. Reaction of II with secondary amines afforded 1-thia-3-azaspiro[5,5]undec-2-enes whereas primary aromatic amines gave 1,3-diazaspiro[5,5]undecanes under the same conditions. Both types of reactions proceed via substituted thioureas which were isolated pure only in the case of 4-methylaniline and 4-methoxyaniline. They were cyclized in alkaline medium to the corresponding diazaspiro derivatives. The structure of the synthesized compounds was confirmed by their elemental analyses and IR, 1H NMR, 13C NMR and mass spectroscopy.

Synthesis, Characterization and Complexation Studies with K + and Ca2+ Cations of trans-1.2-Cyclohexanedioxydiacetamides

1988 ◽  
Vol 43 (2) ◽  
pp. 165-170 ◽  
Author(s):  
Whei Oh Lin ◽  
Maria C. B. V. de Souza ◽  
Helmut G. Alt
Keyword(s):  
Nmr Spectroscopy ◽  
Mass Spectroscopy ◽  
H Nmr ◽  
Coordination Sites ◽  
Complexation Studies ◽  
Ir And Nmr Spectroscopy ◽  
Elemental Analyses ◽  
C Nmr

The synthesis of trans-1.2-cyclohexanedioxydiacetamides starting with trans-1.2-cyclohexane-diol is described. Eleven of these compounds are characterized by IR, 1H NMR, 13C NMR and mass spectroscopy as well as elemental analyses. Most of these compounds are suitable ionophors for the cations K+ and Ca2+. The coordination sites of these ligands in the 1:2 complexes were determined by IR and NMR spectroscopy

New Preparation of 2-N-Alkyl(aryl)amino-5-methyl-4H-1,3-thiazin-4-ones and 3,4-Dihydro-5-methyl-2,4-dioxo-2H-1,3-thiazine

1993 ◽  
Vol 58 (4) ◽  
pp. 893-901 ◽  
Author(s):  
Dušan Koščík ◽  
Milan Dzurilla ◽  
Peter Kutschy
Keyword(s):  
Mass Spectroscopy ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Alkyl Aryl ◽  
New Approach ◽  
H Nmr ◽  
Primary And Secondary Amines ◽  
Sole Product ◽  
C Nmr

Addition-cyclization reactions of 3-bromo- and 3-chloro-2-methylpropenoylisothiocyanates with primary and secondary amines and alcohols have been studied. The formed addition products, thioureas, underwent cyclization of heating with ethanolic KOH or in dimethylformamide in the presence of lithium hydride. This method represents a new approach to 2-dialkyl(aryl)amino-5-methyl-4H-1,3-thiazin-4-ones. Addition reactions with alcohols afforded 3,4-dihydro-5-methyl-2,4-dioxo-2H-1,3-thiazine as the sole product. The structure of the synthesized compounds was confirmed by 1H NMR, 13C NMR, IR and mass spectroscopy.

Heterocycles with a pyrido[3,2-e]-1,3-selenazine and pyrido[3,4-e]-1,3-selenazine ring systems

1983 ◽  
Vol 48 (12) ◽  
pp. 3567-3574 ◽  
Author(s):  
Pavol Kristian ◽  
Dušan Koščík ◽  
Jozef Gonda
Keyword(s):  
Hydrogen Sulfide ◽  
Ring Systems ◽  
H Nmr ◽  
Sodium Hydrogen ◽  
C Nmr

2-Chloronicotinoyl isoselenocyanate (IIa) and 2,6-dimethyl-4-chloronicotinoyl isoselenocyanate (IIb) react with arylamines to give 2-arylimino-4-oxopyrido[3,2-e]-1,3-selenazines IV and 2-arylimino-5,7-dimethyl-4-oxopyrido[3,4-e]-1,3-selenazines V. A reaction of IIa,b with sodium hydrogen sulfide and hydroselenide afford the respective 2-thio- and 2-seleno-4-oxopyrido-1,3-selenazines VI and VII. Structure of these new types of heterocycles was corroborated by spectral (IR, UV, 1H NMR, 13C NMR, and mass) means.

5aH.10aH.15aH-Tribenzo [b.f.j] [1.4.7] trioxa [9 b] azaphenalene - vermeintliche Benzoxete / 5aH, 10aH, 15aH-Tribenzo[b,f,j][l,4,7]trioxa[9 b]azaphenalenes - Supposed Benzoxetes

1979 ◽  
Vol 34 (2) ◽  
pp. 290-296 ◽  
Author(s):  
Herbert Meier ◽  
Ahmed Issa ◽  
Ursula Merkle
Keyword(s):  
Alkaline Medium ◽  
Mass Spectroscopy ◽  
Structure Elucidation ◽  
H Nmr ◽  
Degradation Reactions ◽  
Polycyclic System ◽  
C Nmr

Abstract A supposed benzoxete is determined as a complex polycyclic system: cis,cis,cis-5 aH,10 aH,15 aH-tribenzo[b,f,j][1,4,7]trioxa[9 b]azaplienalene. The structure elucidation is performed by spectroscopycal methods (IR, 1H NMR, 13 C NMR and mass spectroscopy) and by degradation reactions in an acidic or an alkaline medium.

Synthesis of 2-amino-5,7-dimethyl-4-oxopyrido[3,4-e]-1,3-thiazines

1983 ◽  
Vol 48 (12) ◽  
pp. 3426-3432 ◽  
Author(s):  
Dušan Koščík ◽  
Pavol Kristian ◽  
Ondrej Forgáč
Keyword(s):  
Spectral Data ◽  
Chlorine Atom ◽  
Mass Spectra ◽  
High Reactivity ◽  
Secondary Amines ◽  
Dimroth Rearrangement ◽  
H Nmr ◽  
New Synthesis ◽  
C Nmr

New synthesis of pyrido[3,4-e]-1,3-thiazines consisting in reaction of 2,6-dimethyl-4-chloronicotinoyl isothiocyanate with primary or secondary amines, or with benzaldehyde phenylhydrazone, is described. High reactivity of the chlorine atom does not allow isolation of the corresponding thioureas, arising as intermediates, except in the case of the benzylamino derivative. Structure of the products was unequivocally confirmed by their spectral data (IR, UV, 1H NMR, 13C NMR and mass spectra). The synthesized derivatives do not undergo the Dimroth rearrangement.

scholarly journals Design and synthesis of a novel 5-(aminomethylene)thiazolidine-2,4-dione derivatives as potent hepatitis-B virus polymerase inhibitors

2015 ◽  
Vol 10 (2) ◽  
pp. 271
Author(s):  
Wei-Guo Li ◽  
He-Qun Wang
Keyword(s):  
Hbv Dna ◽  
Biologically Active ◽  
Secondary Amines ◽  
Design And Synthesis ◽  
H Nmr ◽  
Viral Antigens ◽  
Polymerase Inhibitors ◽  
Potent Inhibition ◽  
B Virus ◽  
C Nmr

<p>A series of novel thiazolidinedione analogues (TZD) were designed and synthesized potent inhibitors of HBV capsid assembly. The synthesis of thiazolidine-2,4-dione derivatives (4a–4o), starting from the condensation of 5-(ethoxymethylene)thiazolidine-2,4-dione (1) with various secondary amines (3) derived from biologically active compounds. The newly synthesized TZD analogues 4a-4o were characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and MS and evaluated for their anti-HBV activity. Most of the compounds inhibited the expression of viral antigens at low concentration. Six compounds, 4g, 4h, 4l, 4m, 4n, and 4o, demonstrated potent inhibition of HBV DNA replication at submicromolar range. Of these five initial hits, compound 4o was the most active when compared with lamivudine.</p><p> </p><p> </p>

scholarly journals Synthesis of Some Novel Fused Imidazo [2, 1-b] [1, 3] Thiazole and Imidazo [2, 1-b] Thiazolo [5, 4-d] Isoxazole Derivatives

2012 ◽  
Vol 9 (3) ◽  
pp. 1518-1525 ◽  
Author(s):  
Hamid Reza Jaberi ◽  
Hadi Noorizadeh
Keyword(s):  
Acetic Acid ◽  
Sodium Acetate ◽  
Carbon Disulphide ◽  
Thiazole Derivatives ◽  
H Nmr ◽  
Nmr Data ◽  
Elemental Analyses ◽  
New Compounds ◽  
Isoxazole Derivatives ◽  
C Nmr

In this work we describe the synthesis of some novel fused imidazo [2, 1-b] [1, 3] thiazole derivatives. The reaction of 1, 2-diaminoethane 1 with carbon disulphide in H2O/ETOH as solvent furnishes 4, 5-dihydro-1H-imidazol-2-thiol 2 under reflux condition. the reaction of 4,5-dihydro-1H-imidazol-2-thiol on treatment with ethylchloro acetate and aromatic aldehyde in presence of anhydrous sodium acetate and acetic acid as solvent to give (Z)-2-(arylidene)-5,6-dihydroimidazo [2,1-b] [1,3] thiazol-3(2H)-one 3a-j. Compounds 3a-j was condensed with hydroxylamine to give 3-(aryl)-2, 3, 6, 7-tetrahydroimidazo [2, 1-b] [1,3] thiazolo [5, 4-d] isoxazole 4a-j. The structures of the new compounds were established by elemental analyses, IR,1H NMR and13C NMR data.

Synthesen und Reaktionen von schwefelkoordinierten Ruthenium-Komplexen [1]/Syntheses and Reactions of Sulfur Coordinated Ruthenium Complexes [1]

1982 ◽  
Vol 37 (8) ◽  
pp. 1026-1033 ◽  
Author(s):  
Dieter Sellmann ◽  
Elmar Böhlen
Keyword(s):  
Mass Spectroscopy ◽  
Ruthenium Complexes ◽  
H Nmr ◽  
Elemental Analyses

Abstract The syntheses and reactions of sulfur coordinated ruthenium centers with CO, PR3, (R = Me, Ø), N2H4 and N2 are investigated. Reaction of [Ru(CO)3(THF)Cl2] with lithium-o-methylthiobenzenethiolate yields cis-[Ru(CO)2(CH3S-C6H4-S)2], with Li2-o-benzenedithiolate the cis-[Ru(CO)2(C6H4S2)2]2--ion is obtained, which can be isolated either as the NMe4 salt or reacted further with 1,2-C2H4Br2 to give cis-[Ru(CO)2dttd], (dttd2-= 2,3,8,9-Dibenzo-1,4,7,10-tetrathiadecane2-). In all three complexes the CO ligands are relatively inert to substitution; refluxing of [Ru(CO)2(C6H4S2)2]2- in EtOH in the presence of excess PMe3, however, and subsequent alkylation with 1,2-C2H4Br2 yields [Ru(CO)PMe3(dttd)]. [Ru(PMe3)2dttd] is obtained from [Ru(PMe3)4Cl2] and Li2-dttd, the synthesis of which is also described. In [Ru(PMe3)2(dttd)] the PMe3 ligands are inert, but in [Ru(PØ3)2(dttd)] one PØ3 ligand is easily substituted by CO or N2H4 yielding [Ru(CO)(PØ3)dttd] or [Ru(N2H4)(PØ3)dttd] respectively; [Ru(PØ3)2(dttd)] is obtained from [RU(PØ3)3Cl2] and H2-dttd. The complexes are characterized by elemental analyses, IR, 1H NMR and mass spectroscopy.

β-Hydroxydithiozimtsäurederivate als Liganden. Synthese und Charakterisierung neuartiger 1,1-Ethendithiolato- und O,S-Chelatkomplexe / Derivatives of β -Hydroxydithiocinnamic Acids as Ligands. Syntheses and Characterisation of Novel 1,1-Ethenedithiolato and O,S-Chelate Complexes

2007 ◽  
Vol 62 (3) ◽  
pp. 475-482 ◽  
Author(s):  
Karsten Schubert ◽  
Helmar Görls ◽  
Wolfgang Weigand
Keyword(s):  
Bidentate Ligand ◽  
Molecular Structures ◽  
X Ray Diffraction ◽  
Chelate Complexes ◽  
X Ray ◽  
H Nmr ◽  
Hexyl Ester ◽  
Elemental Analyses ◽  
Derivatives Of ◽  
C Nmr

Starting from 4-bromoacetophenone 1, the 4-bromo-β -hydroxydithiocinnamic acid 2 and the 4-bromo-β -hydroxydithiocinnamic acid hexyl ester 3 were prepared using carbon disulfide and potassium-tert-butylate as a base. Acting as a ligand, the acid gives 1,1-ethenedithiolato complexes with (Ph3P)2Pt(II) (4a), (Et3P)2Pt(II) (4b), dppePt(II) (4c), (Ph3P)2Pd(II) (4d), dppePd(II) (4e), and dppeNi(II) (4f). In contrast to the acid, the deprotonated ester 3 forms a monoanionic bidentate ligand. [O,S] Complexes of Pt(II) (5a), Pd(II) (5b) and Ni(II) (5c) were obtained. All complexes have been fully characterised using 1H NMR, 13C NMR and 31P NMR spectroscopy, mass spectrometry, infrared spectroscopy and elemental analyses. The molecular structures of the complexes 4b and 5a - 5c were determined by X-ray diffraction analyses.

scholarly journals Synthesis of compounds related to the anti-migraine drug eletriptan hydrobromide

2012 ◽  
Vol 8 ◽  
pp. 1400-1405 ◽  
Author(s):  
Suri Babu Madasu ◽  
Nagaji Ambabhai Vekariya ◽  
M N V D Hari Kiran ◽  
Badarinadh Gupta ◽  
Aminul Islam ◽  
...  
Keyword(s):  
Mass Spectroscopy ◽  
Acute Treatment ◽  
Selective Serotonin ◽  
Spectroscopic Techniques ◽  
Active Pharmaceutical Ingredients ◽  
Pharmaceutical Ingredients ◽  
H Nmr ◽  
Related Compounds ◽  
C Nmr ◽  
Anti Migraine Drug

Eletriptan hydrobromide (1) is a selective serotonin (5-HT1) agonist, used for the acute treatment of the headache phase of migraine attacks. During the manufacture of eletriptan hydrobromide the formation of various impurities were observed and identified by LC–MS. To control the formation of these impurities during the preparation of active pharmaceutical ingredients, the structure of the impurities must be known. Major impurities of the eletriptan hydrobromide synthesis were prepared and characterized by using various spectroscopic techniques, i.e., mass spectroscopy, FTIR , 1H NMR, 13C NMR/DEPT, and further confirmed by co-injection in HPLC. The present study will be of great help in the synthesis of highly pure eletriptan hydrobromide related compounds.

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